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Real estate in the city of Windermere

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  1. Photo of 13339 Roskin Lane, Windermere, FL 34786 (MLS # S5141148)
    $680,000
    Photo of 13339 Roskin Lane, Windermere, FL 34786 (MLS # S5141148)
    Photo of 13339 Roskin Lane, Windermere, FL 34786 (MLS # S5141148)
    13339 Roskin Lane, Windermere, FL
    13339 Roskin Lane
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 2,947 Home (sqft)
    • 3 Baths
    • 7,406 Lot (sqft)
  2. Photo of 8225 Bryce Canyon Avenue, Windermere, FL 34786 (MLS # O6371960)
    $560,000
    Photo of 8225 Bryce Canyon Avenue, Windermere, FL 34786 (MLS # O6371960)
    Photo of 8225 Bryce Canyon Avenue, Windermere, FL 34786 (MLS # O6371960)
    8225 Bryce Canyon Avenue, Windermere, FL
    8225 Bryce Canyon Avenue
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 1,840 Home (sqft)
    • 3 Baths
    • 5,663 Lot (sqft)
  3. Photo of 5050 Isleworth Country Club Drive, Windermere, FL 34786 (MLS # O6372348)
    $3,390,000
    Photo of 5050 Isleworth Country Club Drive, Windermere, FL 34786 (MLS # O6372348)
    Photo of 5050 Isleworth Country Club Drive, Windermere, FL 34786 (MLS # O6372348)
    5050 Isleworth Country Club Drive, Windermere, FL
    5050 Isleworth Country Club Drive
    Windermere, FL
    • 4 Beds
    • 5 Baths
    • 3,365 Home (sqft)
    • 5 Baths
    • 22,652 Lot (sqft)
  4. Photo of 9725 Chestnut Ridge Drive, Windermere, FL 34786 (MLS # O6370294)
    $6,000,000
    Photo of 9725 Chestnut Ridge Drive, Windermere, FL 34786 (MLS # O6370294)
    Photo of 9725 Chestnut Ridge Drive, Windermere, FL 34786 (MLS # O6370294)
    9725 Chestnut Ridge Drive, Windermere, FL
    9725 Chestnut Ridge Drive
    Windermere, FL
    • 7 Beds
    • 7 Baths
    • 8,000 Home (sqft)
    • 7 Baths
    • 24,394 Lot (sqft)
  5. Photo of 12418 Park Avenue, Windermere, FL 34786 (MLS # O6370377)
    $4,395,000
    Photo of 12418 Park Avenue, Windermere, FL 34786 (MLS # O6370377)
    Photo of 12418 Park Avenue, Windermere, FL 34786 (MLS # O6370377)
    12418 Park Avenue, Windermere, FL
    12418 Park Avenue
    Windermere, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 43,560 Lot (sqft)
  6. Photo of 713 Main Street, Windermere, FL 34786 (MLS # O6368185)
    $2,175,000
    Photo of 713 Main Street, Windermere, FL 34786 (MLS # O6368185)
    Photo of 713 Main Street, Windermere, FL 34786 (MLS # O6368185)
    713 Main Street, Windermere, FL
    713 Main Street
    Windermere, FL
    • 6 Beds
    • 6 Baths
    • 5,031 Home (sqft)
    • 6 Baths
    • 16,118 Lot (sqft)
  7. Photo of 4226 Downeast Lane, Windermere, FL 34786 (MLS # O6367852)
    $10,500,000
    Photo of 4226 Downeast Lane, Windermere, FL 34786 (MLS # O6367852)
    Photo of 4226 Downeast Lane, Windermere, FL 34786 (MLS # O6367852)
    4226 Downeast Lane, Windermere, FL
    4226 Downeast Lane
    Windermere, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 9.03 Lot (ac)
  8. Photo of 13106 Orange Isle Drive, Windermere, FL 34786 (MLS # O6361057)
    $870,000
    Photo of 13106 Orange Isle Drive, Windermere, FL 34786 (MLS # O6361057)
    Photo of 13106 Orange Isle Drive, Windermere, FL 34786 (MLS # O6361057)
    13106 Orange Isle Drive, Windermere, FL
    13106 Orange Isle Drive
    Windermere, FL
    • 5 Beds
    • 5 Baths
    • 3,312 Home (sqft)
    • 5 Baths
    • 6,970 Lot (sqft)
  9. Photo of 2125 Kane Park Way, Windermere, FL 34786 (MLS # O6358139)
    $965,000
    Photo of 2125 Kane Park Way, Windermere, FL 34786 (MLS # O6358139)
    Photo of 2125 Kane Park Way, Windermere, FL 34786 (MLS # O6358139)
    63
     
    2125 Kane Park Way, Windermere, FL
    2125 Kane Park Way
    Windermere, FL
    • 4 Beds
    • 3 Baths
    • 2,743 Home (sqft)
    • 3 Baths
    • 30,928 Lot (sqft)
  10. Photo of 12333 Via Derna Place, Windermere, FL 34786 (MLS # O6362685)
    $449,000
    Photo of 12333 Via Derna Place, Windermere, FL 34786 (MLS # O6362685)
    Photo of 12333 Via Derna Place, Windermere, FL 34786 (MLS # O6362685)
    12333 Via Derna Place, Windermere, FL
    12333 Via Derna Place
    Windermere, FL
    • 3 Beds
    • 3 Baths
    • 1,919 Home (sqft)
    • 3 Baths
    • 2,614 Lot (sqft)
  11. Photo of 6130 Grosvenor Shore Drive, Windermere, FL 34786 (MLS # O6361099)
    $3,150,000
    Photo of 6130 Grosvenor Shore Drive, Windermere, FL 34786 (MLS # O6361099)
    Photo of 6130 Grosvenor Shore Drive, Windermere, FL 34786 (MLS # O6361099)
    6130 Grosvenor Shore Drive, Windermere, FL
    6130 Grosvenor Shore Drive
    Windermere, FL
    • 4 Beds
    • 5 Baths
    • 4,676 Home (sqft)
    • 5 Baths
    • 23,958 Lot (sqft)
  12. Photo of 4415 Blue Major Drive, Windermere, FL 34786 (MLS # O6359496)
    $815,000
    Photo of 4415 Blue Major Drive, Windermere, FL 34786 (MLS # O6359496)
    Photo of 4415 Blue Major Drive, Windermere, FL 34786 (MLS # O6359496)
    4415 Blue Major Drive, Windermere, FL
    4415 Blue Major Drive
    Windermere, FL
    • 5 Beds
    • 3 Baths
    • 3,211 Home (sqft)
    • 3 Baths
    • 6,534 Lot (sqft)
  13. Photo of 9575 Westover Roberts Road, Windermere, FL 34786 (MLS # O6357873)
    $4,850,000
    Photo of 9575 Westover Roberts Road, Windermere, FL 34786 (MLS # O6357873)
    Photo of 9575 Westover Roberts Road, Windermere, FL 34786 (MLS # O6357873)
    9575 Westover Roberts Road, Windermere, FL
    9575 Westover Roberts Road
    Windermere, FL
    • 7 Beds
    • 8 Baths
    • 8,931 Home (sqft)
    • 8 Baths
    • 5.44 Lot (ac)
  14. Photo of 6149 Grosvenor Shore Dr, Windermere, FL 34786 (MLS # O6356355)
    $10,900,000
    Photo of 6149 Grosvenor Shore Dr, Windermere, FL 34786 (MLS # O6356355)
    Photo of 6149 Grosvenor Shore Dr, Windermere, FL 34786 (MLS # O6356355)
    6149 Grosvenor Shore Dr, Windermere, FL
    6149 Grosvenor Shore Dr
    Windermere, FL
    • 6 Beds
    • 8 Baths
    • 6,783 Home (sqft)
    • 8 Baths
    • 2.65 Lot (ac)
  15. Photo of 2958 Marquesas Court, Windermere, FL 34786 (MLS # O6357302)
    $1,855,000
    Photo of 2958 Marquesas Court, Windermere, FL 34786 (MLS # O6357302)
    Photo of 2958 Marquesas Court, Windermere, FL 34786 (MLS # O6357302)
    2958 Marquesas Court, Windermere, FL
    2958 Marquesas Court
    Windermere, FL
    • 5 Beds
    • 5 Baths
    • 4,716 Home (sqft)
    • 5 Baths
    • 1.10 Lot (ac)
  16. Photo of 3328 Wax Berry Court, Windermere, FL 34786 (MLS # O6355868)
    $925,000
    Photo of 3328 Wax Berry Court, Windermere, FL 34786 (MLS # O6355868)
    Photo of 3328 Wax Berry Court, Windermere, FL 34786 (MLS # O6355868)
    3328 Wax Berry Court, Windermere, FL
    3328 Wax Berry Court
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 2,636 Home (sqft)
    • 4 Baths
    • 43,560 Lot (sqft)
  17. Photo of 4226 Downeast Lane, Windermere, FL 34786 (MLS # O6355233)
    $10,500,000
    Photo of 4226 Downeast Lane, Windermere, FL 34786 (MLS # O6355233)
    Photo of 4226 Downeast Lane, Windermere, FL 34786 (MLS # O6355233)
    4226 Downeast Lane, Windermere, FL
    4226 Downeast Lane
    Windermere, FL
    • 5 Beds
    • 3 Baths
    • 5,316 Home (sqft)
    • 3 Baths
    • 9.03 Lot (ac)
  18. Photo of 11162 Ledgement Lane, Windermere, FL 34786 (MLS # O6346461)
    $995,000
    Photo of 11162 Ledgement Lane, Windermere, FL 34786 (MLS # O6346461)
    Photo of 11162 Ledgement Lane, Windermere, FL 34786 (MLS # O6346461)
    11162 Ledgement Lane, Windermere, FL
    11162 Ledgement Lane
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 3,248 Home (sqft)
    • 4 Baths
    • 14,375 Lot (sqft)
  19. Photo of 1361 Whitney Isles Drive, Windermere, FL 34786 (MLS # O6352069)
    $1,200,000
    Photo of 1361 Whitney Isles Drive, Windermere, FL 34786 (MLS # O6352069)
    Photo of 1361 Whitney Isles Drive, Windermere, FL 34786 (MLS # O6352069)
    1361 Whitney Isles Drive, Windermere, FL
    1361 Whitney Isles Drive
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 2,787 Home (sqft)
    • 4 Baths
    • 10,019 Lot (sqft)
  20. Photo of 6712 Thornhill Circle, Windermere, FL 34786 (MLS # O6351284)
    $680,000
    Photo of 6712 Thornhill Circle, Windermere, FL 34786 (MLS # O6351284)
    Photo of 6712 Thornhill Circle, Windermere, FL 34786 (MLS # O6351284)
    6712 Thornhill Circle, Windermere, FL
    6712 Thornhill Circle
    Windermere, FL
    • 5 Beds
    • 4 Baths
    • 2,976 Home (sqft)
    • 4 Baths
    • 6,099 Lot (sqft)
  21. Photo of 5243 Isleworth Country Club Drive, Windermere, FL 34786 (MLS # O6348067)
    $5,100,000
    Photo of 5243 Isleworth Country Club Drive, Windermere, FL 34786 (MLS # O6348067)
    Photo of 5243 Isleworth Country Club Drive, Windermere, FL 34786 (MLS # O6348067)
    5243 Isleworth Country Club Drive, Windermere, FL
    5243 Isleworth Country Club Drive
    Windermere, FL
    • 4 Beds
    • 6 Baths
    • 6,424 Home (sqft)
    • 6 Baths
    • 22,216 Lot (sqft)
  22. Photo of 436 E 7th Avenue, Windermere, FL 34786 (MLS # O6350454)
    $2,175,000
    Photo of 436 E 7th Avenue, Windermere, FL 34786 (MLS # O6350454)
    Photo of 436 E 7th Avenue, Windermere, FL 34786 (MLS # O6350454)
    436 E 7th Avenue, Windermere, FL
    436 E 7th Avenue
    Windermere, FL
    • 4 Beds
    • 5 Baths
    • 3,136 Home (sqft)
    • 5 Baths
    • 32,235 Lot (sqft)
  23. Photo of 9802 6th Street, Windermere, FL 34786 (MLS # O6349678)
    $575,000
    Photo of 9802 6th Street, Windermere, FL 34786 (MLS # O6349678)
    Photo of 9802 6th Street, Windermere, FL 34786 (MLS # O6349678)
    1
     
    9802 6th Street, Windermere, FL
    9802 6th Street
    Windermere, FL
    • 0 Beds
    • 0 Baths
    • 0 Home (sqft)
    • 0 Baths
    • 20,474 Lot (sqft)
  24. Photo of 8724 Peachtree Park Court, Windermere, FL 34786 (MLS # S5135795)
    $839,500
    Photo of 8724 Peachtree Park Court, Windermere, FL 34786 (MLS # S5135795)
    Photo of 8724 Peachtree Park Court, Windermere, FL 34786 (MLS # S5135795)
    8724 Peachtree Park Court, Windermere, FL
    8724 Peachtree Park Court
    Windermere, FL
    • 4 Beds
    • 4 Baths
    • 3,315 Home (sqft)
    • 4 Baths
    • 6,970 Lot (sqft)
  25. Photo of 17538 Black Rail Street, Windermere, FL 34786 (MLS # O6349325)
    $1,390,000
    Photo of 17538 Black Rail Street, Windermere, FL 34786 (MLS # O6349325)
    Photo of 17538 Black Rail Street, Windermere, FL 34786 (MLS # O6349325)
    17538 Black Rail Street, Windermere, FL
    17538 Black Rail Street
    Windermere, FL
    • 6 Beds
    • 5 Baths
    • 4,999 Home (sqft)
    • 5 Baths
    • 9,148 Lot (sqft)
  26. Photo of 6965 Tettenhall Lane, Windermere, FL 34786 (MLS # O6340538)
    $699,000
    Photo of 6965 Tettenhall Lane, Windermere, FL 34786 (MLS # O6340538)
    Photo of 6965 Tettenhall Lane, Windermere, FL 34786 (MLS # O6340538)
    6965 Tettenhall Lane, Windermere, FL
    6965 Tettenhall Lane
    Windermere, FL
    • 5 Beds
    • 3 Baths
    • 3,050 Home (sqft)
    • 3 Baths
    • 6,534 Lot (sqft)
  27. Photo of 13420 Bonica Way, Windermere, FL 34786 (MLS # O6347722)
    $1,875,000
    Photo of 13420 Bonica Way, Windermere, FL 34786 (MLS # O6347722)
    Photo of 13420 Bonica Way, Windermere, FL 34786 (MLS # O6347722)
    13420 Bonica Way, Windermere, FL
    13420 Bonica Way
    Windermere, FL
    • 5 Beds
    • 4 Baths
    • 4,489 Home (sqft)
    • 4 Baths
    • 22,652 Lot (sqft)
  28. Photo of 13448 Bellaria Circle, Windermere, FL 34786 (MLS # O6346484)
    $3,200,000
    Photo of 13448 Bellaria Circle, Windermere, FL 34786 (MLS # O6346484)
    Photo of 13448 Bellaria Circle, Windermere, FL 34786 (MLS # O6346484)
    13448 Bellaria Circle, Windermere, FL
    13448 Bellaria Circle
    Windermere, FL
    • 6 Beds
    • 7 Baths
    • 6,308 Home (sqft)
    • 7 Baths
    • 41,382 Lot (sqft)
  29. Photo of 6102 S Hampshire Court, Windermere, FL 34786 (MLS # O6344907)
    $2,399,000
    Photo of 6102 S Hampshire Court, Windermere, FL 34786 (MLS # O6344907)
    Photo of 6102 S Hampshire Court, Windermere, FL 34786 (MLS # O6344907)
    6102 S Hampshire Court, Windermere, FL
    6102 S Hampshire Court
    Windermere, FL
    • 4 Beds
    • 6 Baths
    • 4,810 Home (sqft)
    • 6 Baths
    • 19,167 Lot (sqft)
  30. Photo of 2 Chase Road, Windermere, FL 34786 (MLS # O6345197)
    $2,200,000
    Photo of 2 Chase Road, Windermere, FL 34786 (MLS # O6345197)
    Photo of 2 Chase Road, Windermere, FL 34786 (MLS # O6345197)
    3
     
    2 Chase Road, Windermere, FL
    2 Chase Road
    Windermere, FL
    • 4 Beds
    • 5 Baths
    • 3,889 Home (sqft)
    • 5 Baths
    • 19,167 Lot (sqft)
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The information contained herein has been provided by My Florida Regional MLS DBA Stellar MLS. IDX information is provided exclusively for consumers' personal, non-commercial use, that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the MLS. Listings last updated 7/1/26 4:38 AM PDT.

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